Synthesis of the C17–C30 Bis-THF Fragment of Iriomoteolide-13a via Intramolecular syn-Oxypalladation of 26-Ene-17,21,23,28-tetraol-Reference-Cited by-同舟云学术

Synthesis of the C17–C30 Bis-THF Fragment of Iriomoteolide-13a via Intramolecular syn-Oxypalladation of 26-Ene-17,21,23,28-tetraol

Published:2023-03-20 Issue:16 Volume:55 Page:2602-2608
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Dai Wei-Min¹,Gao Kai¹²,Ma Haichen¹,Yip Tsz Chun¹,Zhao Hui¹

Affiliation:

1. Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) and Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry, The Hong Kong University of Science and Technology

2. School of Pharmaceutical Sciences, Taizhou University

Abstract

AbstractThe fully substituted C17–C30 bis-tetrahydrofuran fragment of the proposed structure of iriomoteolide-13a has been assembled via asymmetric dihydroxylation-SN2 cyclization of 19-mesyloxy-21-ene-26-yne and PdCl2-catalyzed syn-oxypalladation of 26-ene-17,21,23,28-tetraol as the key steps. The syn-oxypalladation process gave an 89:11 diastereoselectivity and tolerated the free poly-hydroxy groups in the highly functionalized substrate.

Funder

Research Grant Council, University Grants Committee

Southern Marine Science and Engineering Guangdong Laboratory

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-2058-0355.pdf

Reference20 articles.

1. Iriomoteolide-13a, a cytotoxic 22-membered macrolide from a marine dinoflagellate Amphidinium species

2. Synthesis of the C19–C30 bis-THF fragment of iriomoteolide-13a via stepwise SN2 cyclization and intramolecular syn-oxypalladation

3. Stereochemistry and Mechanistic Study of Intramolecular PdII-Catalyzed Oxypalladation and 1,3-Chirality-Transfer Reactions

4. Stereoselective synthesis of contiguous THF–THF and THF–THP units via PdII-catalyzed tandem reaction with 1,3-chirality transfer

5. Construction of Iterative Tetrahydrofuran Ring Units and Total Synthesis of (+)-Goniocin